We are heading down that way from East TN on 4/22. I say "that way" because we are doing a mostly back road trip. It's our 30th anniversary and we have taken the back road trips many times. No hurries. Stop and see what we want whenever we want. We always enjoy hitting the small towns and finding the local best place. We will be there mid week or so.
We are going to spend a couple days there. Need to know what are some of the places to eat or stay away from.

 

Lots of good bars with descent food on Key West. Two places I like that are a little off the beaten path are Schooner Wharf Bar two blocks off of Duvall and Hogfish Bar & Grill on Stock Island. Both are on the water with plenty of outdoor seating.

 

Pepe's in Key West. Miss it and you're missing an institution.

Alabama Jack's on Card Sound Road at the top of the Keys.

 

We will be making a stop at Irish Kevin's.

 

Mile Marker 10, great for breakfast or lunch:
http://www.bobalussoutherncafe.net/

Big Pine Key:
http://www.nonamepub.com/

Mile Marker 49:
http://www.thestuffedpig.com/

For us, Bobalus's is a nice ride off Key West for lunch, sometimes breakfast. No Name, same thing, decent little ride for lunch. Stuffed Pig is our usual stop on the way home, about an hour out of Key West so you feel like you did some traveling before breakfast.

In Key West, good for late night outdoor dinner:
http://www.blueheavenkw.com/

All previous suggestions also great. Hard to find a bad meal in the Keys, they like their food. Try and find any deli/bodega with a line, go inside and get a Cuban sandwich, you will thank me later. Have fun.

 

Taking US 41 all the way through TN, GA and FL, and ending up in Key West, is a ride I've been wanting to do for a long time. It's on my bucket list. Unfortunately, I have other trips competing with it at this time. I look forward to seeing some pictures.

 

Garbos Grill, it is a taco stand behind a bar on Caroline St. just of Duval.

Also like Alonzo's for happy hour.

Sandy's for a cuban sandwich. On white St.

 

We are taking 25 south to south Ga then 301 to St Augustine. Then US1 and some other little side roads. We will be coming back on either part of 27 to 41 or the whole way on 41. It's a coin toss.
My wife is an avid picture taker. I will post some when we get back.

 

Thanks for the tips on eating. The wife usually plans our trips by where to eat.

 

I just found the Hogfish grill on stock island last week. Great food
I always stop at Robbie's Marina for breakfast get a table as close to the boat slips as possible It's a blast watching people feed the tarpon & fighting the pelicans